Stereoselective gold(I)-catalyzed intermolecular hydroalkoxlation of alkynes
Abstract
We report the use of cationic gold complexes [Au(NHC)(CH3CN)][BF4] and [{Au(NHC)}2(μ-OH)][BF4] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows for the use of catalyst loadings as low as 200 ppm for the addition of primary alcohols to internal alkynes (TON = 35 000, TOF = 2188 h-1).
Citation
Veenboer , R M P , Dupuy , S & Nolan , S P 2015 , ' Stereoselective gold(I)-catalyzed intermolecular hydroalkoxlation of alkynes ' , ACS Catalysis , vol. 5 , no. 2 , pp. 1330-1334 . https://doi.org/10.1021/cs501976s
Publication
ACS Catalysis
Status
Peer reviewed
ISSN
2155-5435Type
Journal article
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © 2015 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see: http://dx.doi.org/10.1021/cs501976s
Description
The EPSRC and ERC are gratefully acknowledged for support.Collections
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